Top Vacation homes in Kissimmee

Find the Top Vacation homes in Kissimmee – 50+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-20 out of 52 vacation homes
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10 adults
4 bedrooms
5 beds
MapView on map12.9 mi from City Center
From   US$ 10 /nightSelect
  • On-site H2O water park
  • Full-service spa and wellness center
  • Family-friendly restaurant on-site
MapView on map11.6 mi from City Center
From   US$ 1 480 /nightSelect
  • Infinity pool with stunning views
  • Family-friendly restaurant with seafood
  • On-site water park for kids
  • Outdoor dining
  • On-site spa
  • Exercise gym
3.6 mi from City Center1000 yd from Give Kids The World Village
From   US$ 301 /nightSelect
  • On-site spa for relaxation and wellness
  • Exercise gym for fitness enthusiasts
  • Outdoor dining area with scenic views
  • Outdoor pool
  • Tennis court
  • Game room
4.2 mi from City Center500 yd from Capone's Dinner and Show
From   US$ 121 /nightSelect
  • Exciting on-site water park
  • Heated outdoor swimming pool
  • Tennis court for guests
  • Private Pool
  • Fitness Room
  • Kids' Club
4.2 mi from City Center600 yd from Capone's Dinner and Show
From   US$ 195 /nightSelect
  • Private villa with hot tub
  • Multiple outdoor heated pools
  • On-site spa and wellness center
  • Private Pool
  • Game Room
  • Fitness Center
11.3 mi from City Center
From   US$ 539 /nightSelect
  • Private water park with thrilling slides
  • Luxury homes with private pools
  • On-site dining with gourmet options
  • Private Pool
  • Fitness Centre
  • Game Room
3.7 mi from City Center1100 yd from Kissimmee Value Outlet Shops
From   US$ 331 /nightSelect
  • 8 bedrooms with private pool access
  • Indoor and outdoor swimming pools available
  • Fully equipped kitchen with modern appliances
  • Fitness centre
  • Air conditioning
  • Private entrance
6.2 mi from City Center1.0 mi from Fun Spot America Kissimmee
From   US$ 184 /nightSelect
  • Private entrance for enhanced privacy
  • Fully equipped kitchen for home cooking
  • On-site fitness centre for workouts
  • Private Pool
  • Fitness Center
  • Patio Garden
14.7 mi from City Center
From   US$ 697 /nightSelect
  • Private pool with spa amenities
  • Spacious 9-bedroom accommodation
  • On-site fitness center available
  • Snack bar
  • Jacuzzi
  • Game room
4.2 mi from City Center500 yd from Capone's Dinner and Show
From   US$ 110 /nightSelect
  • Billiards and tennis courts available
  • On-site hot tub for relaxation
  • Picnic area with outdoor dining
  • Outdoor pool
  • Spa centre
  • Mini-golf
5.4 mi from City Center1.2 mi from Capone's Dinner and Show
From   US$ 244 /nightSelect
  • Private outdoor pool for relaxation
  • On-site spa facilities for wellness
  • Activities like fishing and mini-golf
  • Private Pool
  • Fitness Centre
  • Kids Club
14.8 mi from City Center
From   US$ 508 /nightSelect
  • Private pool with wellness packages
  • Indoor play area and kids club
  • Jacuzzi and fitness centre
3.5 mi from City Center1100 yd from Kissimmee Value Outlet Shops
From   US$ 768 /nightSelect
3.5 mi from City Center600 yd from Give Kids The World Village
From   US$ 208 /nightSelect
  • Outdoor pool
  • Flat-screen TV
  • Air conditioning
6.0 mi from City Center1.2 mi from Fun Spot America Kissimmee
From   US$ 517 /nightSelect
  • Outdoor swimming pool open all year
  • Fully equipped kitchen for family meals
  • Air conditioning ensures comfort
  • Private Pool
  • Tennis Court
  • Game Room
14.8 mi from City Center
From   US$ 552 /nightSelect
  • Private pool for relaxation
  • Tennis court for activities
  • Children's playground for families
  • Fitness center
  • Heated pool
  • Free parking
14.7 mi from City Center
From   US$ 813 /nightSelect
  • Heated swimming pool for relaxation
  • Fitness center for active guests
  • Spacious 9-bedroom holiday home
  • Private Pool
  • Hot Tub
  • Game Room
4.0 mi from City Center1.2 mi from Capone's Dinner and Show
From   US$ 276 /nightSelect
  • Private pool and hot tub
  • On-site water park access
  • Five spacious bedrooms
  • 4 Bedrooms
  • Game Room
  • Pet Friendly
3.1 mi from City Center1.1 mi from Osceola County Stadium
From   US$ 1 479 /nightSelect
  • Private entrance for added privacy
  • Year-round outdoor swimming pool
  • Child-friendly play area available
  • Heated Pool
  • Outdoor Dining
  • Golf Course
6.3 mi from City Center1.1 mi from Fun Spot America Kissimmee
From   US$ 144 /nightSelect
  • Outdoor heated swimming pool
  • Full golf course on-site
  • Family-friendly outdoor dining area